My Evolving Transition Ch. 03

My Evolving Transition Ch. 03 (The Bug)

Introduction:

My girlfriend groomed me into participating in gay sex, by getting me hooked on strap-on sex with her. It was all a rouse. Once I had real gay sex and was caught, I was left embarrassed. I felt guilty to face the community, so I fled and took a holiday interstate.

The Story:

The Bug, for gay sex, haunts me.

"I'm going to have you craving cocks and turn you into fag, before you know it," was one of Tiffany's taunts, while nailing my ass with her strap-on dildo. I paid little attention to those taunts back then, as she was turning me on with her strap-on buried deep in my ass. Those were the early warning signs that I ignored.

Back then, I had no idea what my true orientation was, or to have sex with anyone but Tiffany.

I was a sheep and Tiffany was my shepherd, before I knew it, I was craving her to use her strap-on, on me. I hadn't twigged to what she had set in motion, and what was to come.

It all was at that New Year's Eve Party, that her plan was hacked. That's when my world turned upside down. It was when I had gay sex, and at the time loved it. I found out, that while a man had his cock buried inside my mouth, I couldn't help but look up into his eyes. That look, as I milked his cum into my mouth drove me wild with lust. It was a minor distraction while his friend had his cock buried deep in my ass.

I was oblivious to the outside world while this went on, I was in lust for their cocks.

Then my entire world turned on its head. Within an hour, images started appearing on the internet and cell phones, of me covered in cum and engaging in acts of gay sex. Tiffany stopped taking my calls, and soon I twigged why. It was all a nasty plan of hers, she was renowned for breaking boys in her earlier teenage days.

I felt ashamed, and depressed, and locked myself in my loft. I isolated myself from everyone, even my own mother. Here I was in deep regret, on the verge of a breakdown, and contemplating dark thoughts. I knew I needed to get out of town, ASAP.

So, I wrote a letter and left it on my bed for my mother, I then snuck out and caught a bus interstate and planned on doing a tour around the country.

*

My first bus trip out of town was a 4-hour journey to the state's capital. Then once there it was a three-hour delay to board a connecting tourist bus.

So, I spent a few hours window shopping at the Terminus stores. I had a snack to eat and beer in a bar. What I looked at more, was all the girls dressed scantily in the mall. I wished I could dress like them or be them.

Then it was time to catch the bus interstate and to the national park region. I sat in the rear of the bus. That's something I had always done. Nerds sat at the front, and dudes sat at the back. It's something I picked while in High School.

During the first few days of our trip, my thoughts and dreams haunted me. I kept seeing images of cocks and me sucking them, and the New Year's Party, with the Puppet-master Tiffany, watching proceedings like an evil schoolteacher.

While on tour, we ventured thru farmlands, mountains, and the odd town, before staying in a cheap motel for two nights in a big city.

My voyage was only supposed to be for around a month, so I packed light.

It was winter when we left but we were in a warm state, with no snow or rain here. I wasn't planning on staying away for too long, or factor in that altitude brought a colder climate, and I didn't pack for the cold.

In my pack were a few boxers, socks, T-Shirts, a blanket, a towel, plus showering items, as well as the clothes I was wearing. At the time I had gym shoes, socks, Dolphin shirts, boxers, and a tank top T-shirt with a band's logo on it. By the time we had our second stop-over in a big city, it was getting colder. So, I bought a hooded poncho from a thrift store, a raincoat, and patterned yoga pants.

I was still only planning for a month's trip.

So, here I was at the time, wearing Dolphin shorts, gym shoes, and my hooded poncho, and using my blanket as a pillow, while on the bus. I was looking at people, farm animals, and the country scenery, while semi-unconsciously daydreaming about nothing. Only potholes broke my focus.

At times when we were high up in the mountains, it felt colder. So, I wore my raincoat and yoga pants and wrapped myself in my blanket to keep warm.

When we had stopovers or rest stops, we all disembarked to stretch our legs or went to find some food. We had a few hours to kill before we left the area, so there was time to check out the local bars and food shops. I felt ultra cold, wandering outside, so I only went outside briefly before returning to the comfort of a warm bus.

After my second month of touring, we made it to warmer areas and I started looking at women wearing fewer clothes, and I was back to fantasizing about them, and wanting to be them. Also, I was thinking about sex again or sexy things.

After two months of journeying the country and warmer weather, I had gotten used to wearing and walking the outdoors, dressed like a girl dressed casually. I even bought a pair of tanned cowboy boots with an inner zipper, that almost reached my knees, from one of our stops. My hair was slowly starting to grow longer, and it was now shoulder-length. By now I had even purchased a long-sleeved fishnet top.

Ask me why, I don't know myself, why or why I imagined I was a girl. Maybe I was on holiday and it was part of the adventure.

My current booked coach led me to another big city. After three months away from home, I was beginning to feel frisky and started to crave sex, once again. In my frame of mind, I wouldn't say no, to either a girl or a cock.

**

We had a two-night stopover in the next big city, and the first thing I did was head to the nearest bar. I wore my cowboy boots, tassel brown shorts, and a college basketball top, (no boxers, but I wore socks) and headed to the motel bar.

The motel bar I thought was a dive, and so was the motel. So, I walked outside and saw a bar across the road. Without thinking I crossed the road and entered, from the outside I couldn't see inside the venue, as the windows were painted over, with what looked like old hippie art.

When I went inside, there were people scattered in all areas. There was trendy 80's pop music playing, as I looked around until I spotted the bar.

Once there, the bartender gave me a strange stare, as if saying "What on Earth are you wearing?" I ordered a bourbon on the rocks and sat down, on a stool at the bar.

Before I could say anything, a young man/boy quickly sat on the stool next to me. He began to get clingy and rub my upper back.

"My, my, I dig you rags honey, I don't ever remember seeing you here before," he said, in a girly accent.

"I'm not from here, I'm from out of town," I replied.

"Honey, you've stumbled upon the suburb's gay bar," he said, trying to nibble my ear.

It was then it occurred to me, that he was hitting on me.

"I didn't know, I'm staying at the motel across the road, and it looks like a dive," I said.

"Hmm, honey that happens all the time. They either leave in a hurry or leave here happy. What will you do, lover boy?" he said, with a hand under my basketball top, targeting my bulge.

What the hell have I got myself into? I thought to myself while taking a sip.

"Well honey, I see you're hungry to be satisfied. I can welcome you to the bar by giving your cock a good sucking," he said, in a seductive way, with him inside my shorts and rubbing my cock. I started getting aroused but then started to think about it. It's been over two months or so since Tiffany fucked with my head and now this strange boy was too.

"Let me finish my drink and I'll think about it, maybe later," I said, taking another sip.

"All good, Honey, and I'll have you cumming like a train before the night is over," he said and planted a kiss on my lips. He then skipped away like a girl, and sat with a group of like-minded young guys, in a booth.

I just smirked and shook my head.

"Your first time in a gay bar, buddy," the bartender asked.

"We never had anything like this bar or any gay clubs, where I'm from," I said.

"I gathered that. Hey, buddy, if in the future you go to another gay bar, do not wear what you're wearing. Look at them, they might be gay, but in here, most of them, are wolves, and you look like prey," he said.

"Oh, okay. I'm on holiday and just wanted to express my inner self," I answered.

"On a plus side, this is one of the better gay bars I've worked in. Most of the guys are clean and well-behaved. Jacko over there, I wouldn't put too must trust in him, he's been a bit of slut, since his teens," he said.

I took a sip from my bourbon and ordered another.

"That there is Jeremy or Jessa, he's clean, and looks after himself," he said, as he handed me my drink.

Once, I'd finished my drink, I left the bar and went to the dancefloor. I started to dance around to the beat of some disco track, which was almost like a rave song. Basically, moving my feet on the spot and waving my arms in the air, and wiggling my ass around.

To the other regulars, I must have looked like bait to them, dressed the way I was. I was hit on by a few of them before Jessa surprised me from behind.

He reached over from behind and caressed my bare thigh, and soon reached around and rubbed at my bulge. Jessa looked cute and I got an instant hard-on, that it was him after the bartender raved about him.

"Hey honeybuns, looking for action?" he said, snuggling up to me. He had his hands in my shorts in no time. I didn't resist. In no time my cock and balls were out of my shorts and in his hands.

We started smooching while on the dancefloor. He caressed my cock, before stroking it. We faced Jacko and his friend's table, Jessa was sending a message to them, I suppose. I couldn't help but grind my ass back into him and his cock, while he caressed my cock, as it grew larger.

"Oh, good, you want to play," he whispered into my ear.

"You can say, that," I nervously said.

All my trepidations from three months ago were just a memory. I'm in a fag bar and a young fag was getting his way with me.

Here I was on a dancefloor with a younger man gently caressing my cock, facing me towards the booth where Jacko and other likewise fag boys were. He was biting my neck and making me forget my worries and where I was. I was beginning to drift off and go with the flow.

I was acting like some of the girls from my past, lost in love and lust, and starting to lose myself to him. What was I doing, do I have no morals? I started to believe he was going to make me cum soon.

Maybe it was that he was good-looking, and for the first time in months, I was forgetting my hometown dramas.

He soon had my flimsy tassel shorts down to my ankles. I didn't care that an audience was glancing at me or us. Jessa kissed and bit the back of my neck. I closed my eyes and began moaning. Luckily the music was louder than my moans, or my groans when he penetrated my asshole with a finger.

My cock was sloppy with pre-cum, and I was moaning more. I could tell my cock was bleeding pre-cum as I felt the liquid running down my bare inner thighs. It was then, I noticed that the other fag dudes who were dancing near us were now getting it on as well, with their partners.

The bartender said Jessa was clean and a good kid, so I decided to take the risk. Even if he acted like a bit of a sissy boy, he had me hooked.

"Are you staying at the joint across the road," he whispered.

"Yes," I stuttered.

"Do you want to take this to your room, because I so want to fuck you," he said, while he licked and slobbered my neck and ear.

"Yes, yes," I anxiously answered. I want him to fuck me as well.

"We'll grab some booze and make a night of it" he bit my ear.

I stepped out of my fallen shorts between my ankles and picked them up from the ground, and then wrapped them around my arm, like a sweatband or arm guard. We then went to the bar and ordered some takeaway Jack Daniels cans and mini flasks, and I tipped the bartender for the night. All the time, Jessa was pumping his middle finger into my ass, and I was loving it but found it hard not to wimp while I spoke to the bartender. The bartender gave me a naughty wink, as he knew what was going on, and what was about to go on.

Outside the venue we acted like a normal couple, cuddling up to each other, I felt like the female in this partnership, whether I would admit it or not.

Luckily my basketball top was big enough to walk in the darkness to not show the public I was basically nude, with my cock out. If they saw us from behind, that was a different story, with his hand caressing my bare ass.

"I love cock in my ass," Jessa announced.

"So do I," was my response.

We walked across the traffic lights, embracing like lovers and kissing. The world around us would have known, we were two fags if they bothered to look at us.

**

Once inside, we started stripping in a quick fashion.

Jessa looked like he was a gym junkie, with a toned body. His cock was flaccid but looked as big as mine when rock hard. He had tattoos on his chest and upper back.

"Wow, you've got a big package," I said, admiring. He just winked.

He motioned me to my bed and to lay on my back. Then his hand touched my cock and slowly caressed it.

"Ok, honey bud," he said as he leaned down and kissed the tip of my cock. Then proceed to swallow my whole cock down his eager mouth.

I closed my eyes and was moaning in no time. It was a while since I last masturbated or even had sex, so it didn't take long before I started feeling a build-up in my balls. I hadn't realized he was also giving my asshole a good massage with his middle finger.

"Oh god, oh yeah," I moaned, I was close to passing out with pleasure.

As I started to cum, I opened my eyes, to see Jessa, lovingly licking my saliva-coated cock, like an ice cream on a spring day. Until I let go and first hit his face before, he swallowed down on my cock as I kept exploding. He didn't stop there, he kept sucking for a good minute and bit after I had cum.

He then lay next to me while catching his breath. I look down at his cock which was coated in pre-cum but still soft and at half-mast.

While he caught his breath and relaxed, I was fixated on his cock, and eager to play with it, before tasting his cock. So, I crawled over him and started caressing his cock. It slowly grew, and when it reached over seven inches, I slivered down to the floor like a lizard and swallowed as much as I could.

He rose to a seated position, and I felt his hand scuffing my shoulder-length hair and encouraging me to go deeper. When I swallowed the whole thing, I popped my head up and gasped for air. I then began my bobbing motion of sucking down his shaft, then up, then back down.

Jessa let out a few moans, which encouraged me.

"Honeybud, you're pretty good at sucking cock, if you want, you can take my love in your mouth," that's what I planned to do, anyway.

I kept sucking on his now big cock, it was the biggest thing I had sucked, and I loved it. Soon, I felt him swell in my mouth, and I knew he was going to spew inside my mouth.

As he spasmed, squirt after squirt, made me gurgle cum, until I almost choked, before swallowing his love.

When he'd finished and I swallowed what he had. I laid my head on his lap and licked his cock and balls, he stroked my hair almost roughing it up. Then he wriggled away from me and headed to my tiny fridge and grabbed us a can of Jack Daniels and Coke each.

I was left bent over the bed with my arms crossed under my head.

When he returned, he spanked my bare ass, then he slapped his own girly ass with both his hands.

Jessa went back to eating my cock again, and not long after we sat and drank our Jack and Cokes.

"Round two," I asked.

"No, the Superbowl," he answered. Leaving me confused.

He positioned me, face down on top of the bed, with his ass bent over it. He slapped my ass and spread my cheeks apart.

"I want to make love to you and breed you, Honeybud," he calmly announced.

The first thing he did was finger my ass with two fingers, before applying KY or something similar inside my ass. He fucked my ass like this for a short time.

At first, I felt a little pain when he slid a foreign object inside and twilled circles in my hole. In no time that minor pain became warm and pleasant and soothing. The way he did it felt erotic, unlike the smash and bang of the New Year's Party.

When he removed his fingers to apply more KY, he smeared it around the entrance of my hole. My ass felt numb, but my cock could help but go hard.

"It's showtime," he announced.

Even though I desired to be fucked, a little bit of fear still crept in. I saw how big his cock can be.

He moved my legs slightly apart, as butterflies flew in my stomach, in anticipation.

Jessa rubbed KY over his big cock and began rubbing the head of his cock across my asshole. Then the head was gently pushed inside, inch by inch. I grimace a little as it spread my open.

"Relax," he softly said, as he lifted my ass up slightly. Then he inched inside again, then I felt a lightning bolt hit me, as he forced himself deep inside. I let out a groan of pain.

He just let his cock rest inside, while I absorbed the pain. Then he started to inch in even deeper, he kept pulling back and inching in deeper.

I was groaning in pain and pleasure, as he started moving in and out, slowly. He also began to grunt as he was trying to split open my ass, so his cock could breed me without effort.

When he pulled his cock out, thinking I was too tight, I began to whimper.

"Please, I can take the pain," I pleaded.

With that, Jessa pushed inside and started to thump his cock in and out. At first, I thought he was going to injure me, but I held back any complaints.

Within two, maybe three minutes, he had broken my resistance, and my ass was numb to any pain. My cock flopped around as he started to thump in and out of me. Oh god, this was better than last time. I was moaning non-stop, as my arm stretched full length and gripped my bed.

"Oh god, oh fuck, oh fuck me, fuck me harder," I moaned. As he started to give me a good pounding.

"I want your cock to open my ass so wide, any cock can be buried inside it, fuck me, fuck me good," I pleaded and moaned, at the same time.

"Your ass is so tight, it's strangling my cock," he said and let out a tiny laugh. I knew it was a struggle for him, as I felt the torture of him forcing his cock in hard and deep.

He grabbed my hips tight and fucked the resistance from within me.

Jessa smashed into me, deeper and deeper, hard and fast. I started to feel my balls tighten as my limp cock bobbled around between my legs. My breathing turned to constant moans, as I tried to hold on. In the end, I couldn't hold on, as I suddenly began to twitch and then cum hard, as I clinch the quilt on the bed.

I was left panting and moaning, while he broke my ass.